Transcript for From Michelle Obama's humble Chicago upbringing to the White House: Part 1

Chicago? I've traveled all over the world, and Chicago still by far is one of the most beautiful cities. Reporter: We're taking a ride around the old neighborhood and back in time with former first lady Michelle Obama. We're on Jeffery boulevard. This was where the rich kids lived. And then you'll see. We'll cross the tracks. Reporter: Uh-oh. And we'll get in my neighborhood. Reporter: Michelle lavaughn Robinson grew up on the humble side of the railroad tracks in a diverse working class part of Chicago. I, Barack Hussain Obama -- Reporter: The world would come to know her as Michelle Obama, America's first lady. The regal woman with the common touch. ??? We in the spot ??? Reporter: As America's first black first family, the Obamas ushered in a modern era to the white house. We are asking Americans of all ages to give us five ways they're leading a healthier life. Reporter: Diversity filled the inner circles. Healthy initiative vegetable gardens grew alongside rose gardens. I know I'm going to be pulling up some radishes. Reporter: And the sound of young children warmed the family residence once again. So we're crossing the tracks. This is still south shore. This was my walk to school. Across the street I usually met my friend Terry Johnson right in front of that garage. This is my block. Reporter: Three generations of Robinsons lived here on euclid avenue, a home owned by Michelle's great aunt Robbie and uncle Terry. Here, aunt Robbie is holding Michelle when she was an infant. So this is the house. This is my house. Reporter: Wow. And that was -- that's where we lived, upstairs. Robbie and Terry lived downstairs. That was my bedroom. So you see the four windows? But I walk in there and I think, my god, how four people who lived a full life in that little, bitty space up there. Yes, yeah. Up until recently this little apartment was sort of our inheritance. So any time anybody hit on hard times, we'd just move back up there, you know? Reporter: Michelle told me she wouldn't run into anyone she knew, but she did. Oh, my god. It's nice to meet you, Mr. Reed. How's everything going in the neighborhood? Going well. How's miss Robinson? She's good, yeah, yeah. We used to see her all the time. I'll tell her that we saw you. Reporter: See, this is what you're talking about. It's a small town. We sat down together in the current Obama home base just five miles north of where she grew up. It's the house the young family called home leading up to their eventual move to Washington. First of all, hey, everybody. Welcome to my house. Reporter: Michelle Obama's new book, "Becoming" is a very personal look at her life both inside and out of the white house. She says she hopes the candid book generates conversation. Here I am with a lot I want to say. Reporter: Fraser Robinson, a water plant employee, and his wife Marian, a stay-at-home mom, emphasized education and excellence for their two children. For a young Michelle, navigating the bigger world outside her home sometimes felt like speaking a second language. There was one time you write about that I think you were about 10 years old at the time. And your cousin said to you, why do you talk like a white girl? How do you square who you are, where you come from, with where you want to go? Yeah, yeah. It was one of those kind of moments where it was like, "Psh, you're not like us." And it was because of my speech. At this point the viewers who are watching this, there are a lot of people nodding because when you grew up in the neighborhood, you know, you could get your butt kicked going to school if you looked too uppity or if you were studying too hard. So I had to grow up learning these two languages of how do I fit in with my family and my community and still excel? This wouldn't be the first time that my identity would be challenged. You know, where people couldn't figure out who I was with how I talked and what they -- who they thought I should be. Reporter: Her mother Marian Robinson helped Michelle build a sense of self. Marian is known to many for her dedication to family, famously moving into the first modern white house "Mother-in-law suite," there to help her daughter navigate the demands of raising a private family in a very public house. My parents from very early age encouraged us to put our opinions on the table, to ask questions, to question the context of situations. They encouraged us to understand the context. Reporter: They weren't there to prevent you from falling, but to pick you up when you did. You could speak your mind, but you had to be respectful, you know? And if you got out of hand, you got a look. You'd get a spanking. They weren't free-wheelin' parents. They were still black parents. But they believed in teaching us to think for ourselves. Reporter: Michelle's father gave his children a memorable lesson on the dignity of work and true value of hard earned money. My parents were very clear -- you know, we weren't rich. I remember there was a time my -- my brother wanted to understand 'cause he couldn't get something that he wanted. And my my father laid out all the bills, brought home his paycheck in cash and took every bill and put money on top of it to show what it costs and how much he brought in and what was left. They wanted to make it clear. You know, there was money earned and money that went out. Reporter: Always a star student, Michelle thrived in high school, Chicago's first magnet high school, Whitney young. I was nervous about going. I wondered if I was good enough and could I make it in this highly competitive magnet school. Reporter: You write about fooling around with your boyfriend. Oh, which one? Reporter: Oh, well, it was a high school boyfriend. And you even write about smoking pot. Now, you didn't go into great detail, but you -- you did. You could've left that out. So why did you talk about that? That's what I did. That's part of the becoming story. Everybody had something that they had to work through, something that they were figuring out. Why would I hide that from the next generation? Reporter: In the fall of 1981, Michelle entered princeton university's freshman class. She says princeton was "Scary." Fellow students and mentors gave her the confidence to succeed, as she explained in this Instagram post, sharing a young photo of herself in front of princeton's library. It was the first time I had been in a predominantly white situation. So I had to learn how to adjust in this new world of wealth and privilege and kids that I didn't realize had come from prep schools that had prepared them, and I didn't even know the language of that college. What was a syllabus? Never heard of it. Reporter: You really blazed a path for others. We went back to princeton. We spoke with grads, recent grads and people -- You did? Reporter: Yeah, and people -- and young women who are still in school at princeton. And they spoke about the example that you set for them. I want you to hear it -- Oh, robin. Oh, my gosh. Reporter: Yeah, these -- these are your -- It's just incredible walking the paths of princeton, knowing that Michelle Obama was one here. Oh, my gosh. Knowing that Michelle Obama came from, like, a working class family. Like, Michelle Obama's parents didn't, like, come here and she still came, thrived, found her place and had a productive experience at a school like this, it inspired me. And it's just one of the reasons why I applied to this school. They're standing where I was -- oh, of course, you did that -- She's inspiring us today. And the current students are princeton, the people applying to princeton and just every little girl in America today, I don't think she even knows. Thank you just from the bottom of my heart. I can't thank you enough. And I hope to one day be able to convey that in person. But thank you. Oh, my goodness. Have you ever seen her in person? Is she here? Why did you do that? Reporter: I know, I know. I didn't -- we did feel bad at that point 'cause she thought -- Like she's going to come out -- Reporter: How does that make you feel when you see these young women who said that, because of you, they're there? Yeah, it's -- yeah. So what'd you do that for, robin? It feels, you know, I'm -- I'm glad. I'm glad that they -- Reporter: You proud? Yeah.

This transcript has been automatically generated and may not be 100% accurate.

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